U.S. Pat. No. 4,590,231 describes the use of hydroxylamines, particularly N,N-dibenzylhydroxylamine, as process stabilizers in the presence of costabilizers, such as phenolic antioxidants, in polyolefin compositions. N,N-Dioctylhydroxylamine is disclosed and the longer chain N,N-dialkylhydroxylamines are mentioned generically.
Poly(phenylene sulfide) has become an important polymer of commerce useful in a variety of end-use applications requiring high-performance polymer properties. This involves increased risk of polymer degradation during processing and the need for adequate process stabilizers to prevent the potential polymer degradation.
U.S. Pat. Nos. 4,434,122 and 4,543,224 describe the stabilization of arylene sulfide resins using phenolic amide or ester-based antioxidants.
Evidence that the stabilization of arylene sulfide polymers has been a problem for a long time is seen by the many attempts to find an adequate stabilizer for the processing of the resins. U.S. Pat. No. 4,405,745 describes the use of alkaline earth nitrites; U.S. Pat. No. 4,411,853 teaches the use of dialkyltin dicarboxylates; U.S. Pat. No.4,412,062 describes the use of phosphites, phenolic antioxidants and thiophthalimides; U.S. Pat. No. 4,413,081 teaches the use of Group 8 metal dihydrocarbyldithiocarbamates; U.S. Pat. No. 4,418,029 describes the use of Group IIA or IIB metal salts of fatty acids; and U.S. Pat. No. 4,478,969 teaches the use of aminotriazoles as stabilizers for the arylene sulfide resins.
U.S. Pat. No. 3,432,578 describes the stabilization of conjugated diene polymers against the adverse effects of ultraviolet llight by use of diarylhydroxylamines or of diaralkylhydroxylamines.
U.S. Pat. No. 3,408,422 describes the stabilization of unsaturated polyester compositions using various hydroxyl amines. N,N-Dialkylhydroxylamines of 1 to 12 carbon atoms are generically described. Only N,N-diethylhydroxylamine, N-methyl-N-amylhydroxylamine and N,N-dibutylhydroxylamine are mentioned.
U.S. Pat. No. 3,644,244 describes the use of hydroxylamines including the N,N-dialkylhydroxylamines as stabilizers to prevent the gelation of organosols of butadiene/acrylonitrile graft copolymers. N,N-Dialkylhydroxylamines of 2 to 12 carbon atoms are generically disclosed, but only N,N-diethylhydroxylamine is specifically mentioned.
U.S. Pat. No. 4,242,224 describes the use of dialkylhydroxylamines to reduce or retard the pink discoloration found in amine antioxidant and antiozonant emulsions used in the rubber industry. N,N-dialkylhydroxylamines of 2 to 12 carbon atoms are again generically disclosed, but only N,N-diethylhydroxylamine is specifically mentioned.
U.S. Pat. No. 4,316,996 pertains to the use of hydroxylamine compounds which can prevent the discoloration of phenolic antioxidants in rubber compositions. N,N-Dialkylhydroxylamines of 1 to 18 carbon atoms are generically described, but once again only N,N-diethylhydroxylamine is specifically mentioned.
U.S. Pat. No. 4,547,532 pertains to the use of hydroxylamines to prevent the premature increase in viscosity of polymer-based antifouling paints containing an organotin compound. N,N-Dialkylhydroxylamines of 1 to 20 carbon atoms are generically described, but only N,N-dimethylhydroxylamine, N,N-diethylhydroxylamine and N,N-dibutylhydroxylamine are specifically disclosed.
U.S. Pat. No. 4,409,408 discloses the use of N,N-dialkylhydroxylamines and tertiary alkylcatechols in stabilizing vinyl aromatic compounds, such as styrene, against premature polymerization. N,N-Dialkylhydroxylamines of 2 to 10 carbon atoms are generically disclosed. N,N-Didecylhydroxylamine is specifically mentioned, but not exemplified and the preferred N,N-dialkylhydroxylamines are of 2 to 6 carbon atoms.
None of these references describes the long chain N,N-dialkylhydroxylamines of 12 carbon atoms or more nor does any of said references suggest that the long chain N,N-dialkylhydroxylamines of the instant invention exhibit special properties not possessed by the lower alkyl N,N-dialkylhydroxylamines which are the preferred embodiments in the cited prior art.